The stereoselective total synthesis of (+)-18-(6 S,9 R,10 R)-bovidic acid

Abstract

An expedient stereoselective total synthesis of 18-carbon (+)-(6 S,9 R,10 R)-bovidic acid, isolated from the pelage and skin of a gaur B. frontalis is described using l-proline catalysed sequential α-aminoxylation and Horner–Wadsworth–Emmons olefination of aldehyde, cross metathesis and tandem Sharpless asymmetric dihydroxylation-S N2 cyclization reaction as the key steps.